1. Field of the Invention
This invention relates to certain cycloalkanones, cycloalkanols and unsaturated analogs thereof having from 5 to 8 carbon atoms in the cycloalkyl ring and at the 3-position a 2-hydroxy-4-(Z-W-substituted)phenyl group wherein Z is alkylene having from one to thirteen carbon atoms or (alk.sub.1).sub.m --O--(alk.sub.2).sub.n --wherein each of m and n is 0 or 1 and each of (alk.sub.1) and (alk.sub.2) is alkylene having from one to thirteen carbon atoms with the proviso that summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than thirteen; and W is hydrogen, phenyl, chlorophenyl, fluorophenyl or pyridyl; derivatives thereof, intermediates therefor and processes for their preparation. The products are useful as CNS agents, especially as analgesics, tranquilizers, sedatives and antianxiety agents in mammals, including man, and/or as anticonvulsants, diuretics and antidiarrheal agents in mammals, including man.
2. Description of the Prior Art
Despite the current availability of a number of analgesic agents, the search for new and improved agents continues, thus pointing to the lack of an agent useful for the control of broad levels of pain and accompanied by a minimum of side-effects. The most commonly used agent, aspirin, is of no practical value for the control of severe pain and is known to exhibit various undesirable side-effects. Other analgesic agents such as d-propoxyphene, codeine, and morphine, possess addictive liability. The need for improved and potent analgesic agents is, therefore, evident.
U.S. Pat. No. 3,576,887, issued Apr. 27, 1971, describes a series of 1-(1'-hydroxy)alkyl-2-o-hydroxyphenylcyclohexane or -ene compounds which serve as intermediates for production of 6,6-dialkyltetrahydro- and hexahydro- dibenzo[b,d]pyrans of use as central nervous system depressants.
U.S. Pat. No. 3,974,157 describes 2-phenylcyclohexanones as intermediates for preparation of 1-(aminoalkyl)-2-phenylcyclohexanols useful as analgesics, local anesthetics and antiarrhythmics. The 2-phenylcyclohexanones can be substituted in the phenyl ring with up to two alkyl, hydroxy or alkoxy groups.
Chemical Abstracts 85, 176952f (1976) discloses a number of 3-phenyl- and 3-phenalkylcyclohexanones as intermediates for 2-aminomethyl-3-phenyl (or phenalkyl)-cyclohexanones which exhibit analgesic, sedative, antidepressant and anticonvulsant activities.